Molecular Recognition via Electrostatic Potential Topography

Gadre, Shridhar R.; Bhadane, Pravin K.; Pundlik, Savita S.; Pingale, Shirish S.

doi:10.1016/s1380-7323(96)80045-8

Cited by 32 publications

(24 citation statements)

References 84 publications

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“…The molecular electrostatic potential (MESP) of the pure MOF was calculated, where Z A and R A are the charge and position of nucleus A , respectively; the sum is over all nuclei of the system, and ρ( r ) is the electron density. V ( r ) comprises the bare nuclear potential and the electronic contributions and thus sheds light on the effective localization of electron-rich regions in the molecular system.…”

Section: Computational Methodsmentioning

confidence: 99%

Molecular Interactions of a Cu-Based Metal–Organic Framework with a Confined Imidazolium-Based Ionic Liquid: A Combined Density Functional Theory and Experimental Vibrational Spectroscopy Study

et al. 2016

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The interactions between a Cu-based metal−organic framework (MOF), Cu-BTC, and an ionic liquid (IL), 1-ethyl-3methylimidazolium ethyl sulfate, were studied by employing density functional theory (DFT) calculations and vibrational spectroscopy. The Fourier transform infrared (FTIR) and Raman spectra show that the confinement of the IL in the MOF has significant impact on the structure of the MOF as well as on the IL. Raman spectra and DFT calculations reveal a perturbation of the symmetry of the MOF structure due to the interaction of the IL anion with the Cu ions. FTIR and Raman spectra show that the molecular interactions in turn influence the structure of the ion pair. Inside the MOF, two different types of structure of IL ion pairs are formed. One ion-pair structure exhibits enhanced interionic interactions by strengthening the hydrogen bonding between cation and anion, whereas the other structure corresponds to weaker interactions between the IL cation and anion. Moreover, it is shown that the IL imidazolium ring can directly interact with either the MOF or the anion. The difference electron density analysis by DFT calculations indicates that molecular interactions of MOF and IL are accompanied by a transfer and redistribution of electron density.

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Section: Computational Methodsmentioning

confidence: 99%

Molecular Interactions of a Cu-Based Metal–Organic Framework with a Confined Imidazolium-Based Ionic Liquid: A Combined Density Functional Theory and Experimental Vibrational Spectroscopy Study

et al. 2016

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“…An anisotropic electric field, formed by approaching molecules, orients them to minimize the energy of charge–charge and dipole–dipole interactions10 before an overlap of the VDW radii of their atoms occurs 11a–11c. Therefore, for the early reaction stages of nucleophile 1a –electrophile 3 interactions, an assessment of charge distribution‐related properties12 – that is, molecular electrostatic potential (MEP) as well as dipole moments – could lead to selection of a favored orientation of the reagents 13.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Induction by a Remote Chiral Substituent – Computationally Determined Stereodifferentiation in Michael Additions of α‐Lithiated Allyl Sulfones

2007

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The mechanism of stereoselectivity has been elucidated for the formation of two stereogenic centers in the products of Michael addition to ethyl crotonate by lithiated α-anions of allylic sulfones bearing a remote chiral N-substituent. In order to single out reactive carbanion structures, their conformational analysis was performed by ab initio calculations, finally at the B3LYP/6-31+G(d) level. Low-energy reactant structures were aligned taking intermolecular steric contacts into account. It appeared that only two cyclic conformers of the sulfone nucleophile in which the Li cation is chelated by the anionic carbon, as well as the S=O and NH moieties, are

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“…For instance, (3,À3) refers to a CP with three nonzero negative eigenvalues, i.e., a maximum (or a peak) in the ED distribution function. The application of the AIM theory to other 3D properties, such as molecular electrostatic potentials (MEP), has been proposed by Gadre et al 31 and Leboeuf et al 32 MEP, a wellknown property of a free molecule for examining its reactivity toward electrophiles, is derived from its molecular ED A (r) as follows:…”

Section: Introductionmentioning

confidence: 99%

“…Gadre et al 31 used MEP topology as a predictive tool for obtaining intermolecular interaction parameters. Leboeuf et al 32 showed how MEP CPs are related to the electronic structure ( bonds, lone pairs, etc.)…”

Section: Introductionmentioning

confidence: 99%

Similarity measures based on Gaussian‐type promolecular electron density models: Alignment of small rigid molecules

Leherte

2006

J Comput Chem

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Various molecular similarity measures (overlap, Coulomb, kinetic, electrostatic energy) and similarity indices (Carbó, Hodgkin-Richards, Kulczynski, Shape Tanimoto) are applied to the superposition of 3D promolecular electron density (PED) distributions. The original aspect of the paper lies in the consideration of smoothed PEDs, which allow to decrease the number of local solutions to a superposition problem, together with the use of the less common kinetic and electrostatic energy similarity measures. Results are obtained for a family of five rigid endothiapepsin ligands that were already considered in previous applications, based on graph representations of their PED. In the present work, it is observed that the use of smoothed PED and the kinetic similarity measure, together with the Kulczynski or Shape Tanimoto index, performed the best to align molecules of different sizes.

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Molecular Recognition via Electrostatic Potential Topography

Cited by 32 publications

References 84 publications

Molecular Interactions of a Cu-Based Metal–Organic Framework with a Confined Imidazolium-Based Ionic Liquid: A Combined Density Functional Theory and Experimental Vibrational Spectroscopy Study

Molecular Interactions of a Cu-Based Metal–Organic Framework with a Confined Imidazolium-Based Ionic Liquid: A Combined Density Functional Theory and Experimental Vibrational Spectroscopy Study

Asymmetric Induction by a Remote Chiral Substituent – Computationally Determined Stereodifferentiation in Michael Additions of α‐Lithiated Allyl Sulfones

Similarity measures based on Gaussian‐type promolecular electron density models: Alignment of small rigid molecules

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